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A kind of improved method of pomalidomide synthesis process

A pomalidomide and synthesis process technology, applied in the field of pomalidomide preparation, can solve the problems of long process route, large environmental pollution, solvent residue, etc.

Active Publication Date: 2020-07-07
CHANGZHOU PHARMA FACTORY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This improved process overcomes the shortcomings of low yield, long process route, and large environmental pollution in the prior art, and at the same time solves the problem of solvent residue in the refining process

Method used

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  • A kind of improved method of pomalidomide synthesis process
  • A kind of improved method of pomalidomide synthesis process
  • A kind of improved method of pomalidomide synthesis process

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Pump N,N-dimethylformamide (50kg) into the reactor, add glutamic acid (32kg) and 3-nitrophthalic anhydride (40kg) under stirring, then heat, at 95-100 ℃ for 3 hours, then distill N,N-dimethylformamide under reduced pressure, add acetic anhydride (50kg) under cooling, heat to 100-110℃ for 1 hour, distill off excess anhydride under reduced pressure, add DMSO (400L) , heat the reaction to 200°C, and slowly introduce ammonia gas under stirring. After the reaction, cool to room temperature and add methanol (800L), crystallize and centrifuge, and dry to obtain 3-nitropomalidomide (62.76kg) , yield 71%. 99.99% purity.

[0031] 3-Nitropomalidomide (30kg) was dissolved in 1,4-dioxane\methanol=300L\300L, added 10% palladium carbon, 35°C, 0.4M, hydrogenated until the reaction was complete, press-filtered, and reduced Concentrate to dryness under pressure, add DMF (300L) to dissolve, crystallize from isopropyl ether (600L), centrifuge to obtain a yellow product, and then use etha...

Embodiment 2

[0033] Pump pyridine (50kg) into the reactor, add glutamic acid (32kg) and 3-nitrophthalic anhydride (40kg) under stirring, then heat, react at 95-100°C for 5 hours, and then depressurize Evaporate pyridine, cool and add acetic anhydride (50kg), heat to 100-110°C to react for 2 hours, evaporate excess anhydride under reduced pressure, add DMSO (400L), heat the reaction to 180°C, and slowly introduce ammonia under stirring After the reaction, cool to room temperature, add ethanol (800L) to crystallize and centrifuge, and dry to obtain 3-nitropomalidomide (62.76kg), with a yield of 71% and a purity of 99.2%.

[0034] 3-Nitropomalidomide (30kg) was dissolved in 1,4-dioxane\methanol=150L\150L, ​​added 10% palladium carbon, 35°C, 0.4Mp, hydrogenated until the reaction was complete, press-filtered, reduced Concentrate to dryness under pressure, add DMF (300L) to dissolve, crystallize from isopropyl ether (600L), centrifuge to obtain a yellow product, and then use ethanol to recrysta...

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PUM

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Abstract

The invention relates to a preparation method of pomalidomide of high purity suitable for industrial production. 3-nitrophthalic anhydride and glutamic acid are reacted in order to obtain an intermediate, a reaction is carried out in the condition with acetic anhydride in order to obtain an intermediate, 3-nitro-N-(2,6-dioxo-3-piperidyl)phthalimide is obtained by an ammonification reaction in the DMSO condition, and palladium on carbon is used for hydrogenation in order to obtain pomalidomide. The process has the characteristics of high yield, simple operation, environmental friendliness, large scale production, and the like; a low toxicity solvent is used in order to solve the problem that products are not qualified due to solvent residues.

Description

technical field [0001] The present invention relates to a preparation method of pomalidomide (formula I) with optimized synthesis conditions. [0002] Background technique [0003] Pomalidomide is a thalidomide analogue with antitumor activity, which can inhibit the proliferation of hematopoietic tumor cells and induce apoptosis. In addition, pomalidomide can inhibit the proliferation of lenalidomide-resistant multiple myeloma cell lines, and can cooperate with dexamethasone to induce tumor cell apoptosis, enhance the immune response mediated by T cells and natural killer cells, and inhibit Nuclear cells produce pro-inflammatory cytokines. Pomalidomide was developed by Celgene in the United States and was approved by the FDA in February 2013 for the treatment of multiple myeloma (Multiple Myeloma) ineffective for other drugs (such as lenalidomide and bortezomib). . [0004] Pomalidomide (pomalidomide) is the third lidomide drug after Thalidomide (Thalidomide) and Lenal...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 周付潮董书茂金晓峰
Owner CHANGZHOU PHARMA FACTORY
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